Water → (3S,8S)-3-(4-Hydroxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid methyl ester

HRID 391800Notes

Reaction equation

HRID 391800 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:14][C:13]2[CH:12]=[C:11]3[O:15][CH2:16][C@H:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25]C(=O)C)=[CH:21][CH:20]=4)[O:18][C:10]3=[CH:9][C:8]=2[CH2:7][N:6]1[C@H:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:30][CH3:31])=[O:4].C([O-])(O)=O.[Na+].O>CO>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:14][C:13]2[CH:12]=[C:11]3[O:15][CH2:16][C@H:17]([C:19]4[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=4)[O:18][C:10]3=[CH:9][C:8]=2[CH2:7][N:6]1[C@H:29]([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:30][CH3:31])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 58327394(3S,8S)-3-(4-Acetoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid methyl ester

Product 1

HCID 58327439(3S,8S)-3-(4-Hydroxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3S,8S)-3-(4-Acetoxy-phenyl)-7-((S)-1-phenyl-propyl)-2,3,6,7,8,9-hexahydro-[1,4]dioxino[2,3-g]isoquinoline-8-carboxylic acid methyl ester (120 mg) was dissolved in methanol (5 mL). To this solution was added NaHCO3 (400 mg). The mixture was stirred at rt for 2-3 h. After completion of the reaction, the mixture was poured into water (10 mL) and was extracted with EtOAc (30 mL). The organic layer was washed with water, brine, dried and concentrated to get the desired product as a white solid (110 mg) LCMS (m/z): 461.

Workup

  1. customAfter completion of the reaction
  2. extractionwas extracted with EtOAc (30 mL)
  3. washThe organic layer was washed with water, brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-445e49dfc6264bd2bd687f5020c52c4c
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

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